FWBs Ch. 01: The First Time

"I've been thinking," she says, "I think we should talk about being FWBs." She pauses for a minute as she looks over at me and then continues, "You know, friends with benefits?"

My mind is screaming, "Oh fuck yeah, let's go, I'm in," but I calmly look at her and say, "Ummm... Excuse me?"

She explains, "Friends with benefits, you know, fuck buddies. A simple sexual relationship without the strings attached of being committed or a couple's thing. No expectations of it turning into something more. Just sex."

My mind is still trying to catch up with what I just heard, so I am trying to remain cool, calm, and collected and not blow it by being too eager.

This may be a good time to give you some background info so you can catch up, too.

We both work as buyers at a very famous grocery store chain, but in different departments. So we come in very early in the mornings, I at 4 am, she at 5 am, to shoot the orders. I would guess that no one would suspect that the two of us would ever be having this discussion, much less go through with it.

ME: I am in my mid-50s and was married for about 20 years. My wife started a personal spiritual journey (her words, not mine), which included her giving up sexual pleasures, and we got a divorce about 5 years ago. I am in pretty good shape for my age, and most people are surprised to find out that I am as old as I am. I bike 100-plus miles a week, eat relatively healthy and don't drink alcohol or soda and that helps me to look a little younger than I am. I suppose average looking and have been told several times by women that my easy-going manner, compassionate attitude, and genuine caring make me more attractive as they get to know me.

HER: She is early 30s, and got a divorce about a year and a half ago when she came home from work one day to find her husband moving out to live with his girlfriend. Shocked, she says, doesn't describe the surprise of it. She is long and lean with an athletic body and killer legs, looks like she could have been a swimmer, or a distance runner, or a volleyball player, that type of long lean look. She has one of those cute firm round butts that you just want to grab and is usually encased in a tight pair of jeans. She wears her hair at work in a cheerleader-like ponytail tail but when she lets it loose, it is slightly curly?, wavy?, which gives her a bit more of a wild look. She has small breasts but must have great nipples as there are times in the store that I can see them pushing out against her t-shirt even though she has a bra on. She is sweet and kind and doesn't realize how beautiful she is. She has that girl-next-door look, everyone's best friend kind of thing, you know, attractive without being unapproachable. Almost every guy she talks to turns into a puppy dog, staring at her and begging for more attention. More than once, I have wondered what this woman would be like in bed... and now this?

I had been a buyer for about 10 years when she got promoted to be a buyer for another department. She began asking me lots of questions as she was learning the ropes. The relationship has been a professional mentoring one. She would sometimes tease me by calling me "Old Man" when she would help me with some of the new technology that seemed to always be infiltrating our company, or especially when she would name some current celebrity or movie that I had never heard of. I would call her "Kid" when I mentioned a movie or actor or band that she didn't know because she is so young. There has been some occasional innocent flirting from time to time, knowing that nothing was ever expected to be acted on. But the teasing and flirting also helped her build some of her confidence back that had been so poorly trampled when her husband left.

She came home one day to find her husband loading his stuff into his car, and to add insult to injury, the girl he was moving in with was there with him. He dumped on her pretty bad, telling her that she was cold, terrible in bed, and that he had been having an affair for almost a year. She took a couple of days off, and when she came back to work, I could see the weight of her dealing with being abandoned and the impending divorce. I shared with her about my divorce, how I wasn't expecting it, and even though I could see my wife changing, I was still unprepared for when she said that she wanted a divorce. We have gone our separate ways and haven't had any contact with each other in years. Some things are not meant to be, others are what they are. So move on and find out what's next.

"So what do you think? I hope I didn't insult you or put you in an uncomfortable situation," she so innocently states.

I snap back to reality, realizing in my mind I have already agreed to her request and have started to make plans of where to go and what we are going to do. And that we will be having the best sex of my life. "What? Uummm.. no, I definitely am not insulted, in fact, I am highly flattered that you would even think of me that way. Who wouldn't want to be with someone as beautiful and sexy as you?" I turn my head towards the door to make sure no one has shown up and is listening in.

"You're so silly. Most of the women here talk about how kind and thoughtful you are, and more than one of us has wondered how well you can use those hot bike legs in bed. So, do you think you are up for it?"

"Of course I am up for it." I quickly snap back and am surprised that I feel the need to defend myself. I unconsciously look down at my hard uncomfortable dick. I look up to see that she has also looked at the front of my pants and can see that I am hard. I look back at her and ask, "How do you see this working? Have you thought about it? Rules or guidelines, that sort of thing?"

She says. "Well, I have been thinking about asking you for a while now. I haven't really thought much past seeing what you would say. IF, and it's a big if, you said yes, I think we should try it one time to see if we both, ummm..." she stumbles to find the right words, "uhhh, get along, I mean ummm... enjoy it,... fit? Not quite sure how to phrase it, and then if we like it, we could talk through the details of continuing. If it's not a good fit, then we just agree to go on as if nothing happened."

"That seems like a good plan. When do you see this happening?" I ask.

She immediately replies with, "Well, if we wait too long, we might overthink it and back out or ruin it. What are you doing after work today? Got any better plans than me?"

I am completely flabbergasted at how this shy, quiet little beauty suddenly has this incredibly sexy woman coming out. It is so totally unexpected. I stammer, tripping over my tongue. "Sure, I could make myself available." And I immediately realize that I may have just given the worst comeback ever for being invited to fuck a gorgeous woman.

She smiles at me and in one of the sexiest voices I have ever heard, she seductively whispers, "Do you want me? Have you ever thought about how I look naked? What's it like to have sex with me?"

Well, now I am uncomfortable. My dick is trying to tear through my pants it is so hard. Still trying to remain cool and in charge, even though all I want to do is grab her and tear her clothes off and fuck her right there on the desk, I look her in the eyes and say, "There is nothing in the world I want to know more today than that."

She smiles at me and says, "Wonderful!! My place or yours?" After a brief conversation, we decide it would be better to go to her place for the first time. She lives in an apartment not too far from work. "Meet me in the parking lot right after work. Don't be late."

"Wouldn't think of it?" I respond and start thinking of a way so we could go right now without drawing too much attention to both of us leaving at the same time. To say the next few hours seemed long was an understatement. It felt like it was a couple of weeks or even a month, it went by so slowly. I did have a couple of people comment on my good mood. All I could do was look at the clock and think, Hurry up, damnit.

Finally, quitting time and I hurry out to the parking lot, trying not to sprint. I get there first, but I only have to wait a minute or so before I see those long legs striding down the walk towards me. The closer she gets the more I smile and start thinking about how lucky I am hope and I don't screw this up somehow.

"Good, you didn't chicken out, but I didn't think you would." She gives me a look that is part smile, part challenge. "Follow me, it's about 10 minutes from here." We get in our cars and off we go. We arrive and as we are getting out of our cars, she looks at me and says, "I am so looking forward to this. It has been awhile and I am really hoping that I am right, and that you know how to show a lady a good time. Think you can rock my world?" she spins and leads the way up the few steps and in we go.

I close the door behind me and turn around to look at her apartment, thinking she is going to show me her place and talk a little before we slowly move into whatever it was we are about to do. But as soon as I turn back around to face her, she kisses me rather hard, forces her tongue into my mouth a couple of times, then drops to her knees in front of me. I am so stunned and unsure of what is going I can't respond. She unzips my pants, pulls out my dick and starts giving me what I would a call passionate-less blowjob. Not sure there is such a thing as a bad blowjob, but this was close.

At first, I am shocked at how fast she has moved and think how excited she must be. But as I catch up I realized that this blowjob is rather mechanical, uninspired. As I look down she is holding my dick with one hand and was trying to take off her shirt with the other. I reach down and gently grab her arms and stand her up. "What are you doing?" I gently ask her. "Is this how you want this to go? So fast?" She looks up at me with what I would call a rather surprised look on her face. "And the bigger question is, are you enjoying it?"

Still with a deer in the headlights look, she says, "I figured this is what you would want. This is the way my ex and I would do it. I would blow him for a minute or two and then he would fuck me until he came" she explains.

I smile at her and softly reply, "Let's go sit on the couch for a moment and talk." I help her pull her shirt back down and then lead her over to the couch. "I want to talk with you first, find out what you like and don't like when it comes to sex. What makes you feel good? And how can we make this enjoyable for both of us."

She looks at me like I have just tried to explain quantum physics to her. In a very meek voice (which surprised me), she says, "I thought maybe you had changed your mind and decided you didn't want me."

"Are you crazy? Who wouldn't want you? I am dying to make love to you, or have sex, or whatever FWBs call it." I tell her. The smile comes back to her face for a moment.

She explains that her sexual life/experiences with her husband was nothing to brag about. "We always did pretty much the same thing the same way. It would start with me sucking his dick, sometimes he would be standing up and sometimes he would sit in the chair. After he was ready, we would take off our clothes and he would fuck me, (she barely said the work fuck, almost in a whisper), usually on top of me, and towards the end of our marriage only from behind, doggy style."

I am looking at this meek, quiet, rather defeated woman and begin to understand what has happened to the confident, always in control fireball that I work with. "Did you enjoy it? Did you have an orgasm? What did you like that he did to you?"

Her eyes drop down and she says, "I don't think I ever had an orgasm with him, every once in a while I would masturbate, I sometimes had one then. He told me it was my fault that I didn't cum when I was with him. He said if he could cum then so should I."

I reach down and put a finger under her chin to tilt her head up till her lips are close to mine. I lean in and kiss her. First, gently with soft caressing kisses. As she relaxes, I increase the intensity until we start exchanging tongues. I start to get a few muffled moans out of her, and I pull her over on top of me so she is straddling my lap. We continue to kiss a little longer.

When I feel that she is finally starting to relax, and is fully present with me, I stop kissing her for a moment and say. "Before we go any further, I think some basic rules and agreements are in order. First and foremost, I don't want you to do anything that doesn't feel good and bring you pleasure. Second, either of us can stop things whenever we want or need to. Third, this is about us enjoying each other and having a good time. Agreed?" She nods her head yes. I put my hand behind her neck and pull her in for another session of big, wet, sloppy kisses, and get some more moans.

I am running my hands down her back and across her butt, then down the side of her legs and them back up. She is starting to grind against me. She stops the kissing this time and asks, "What do you mean you want to know what I like? Why would you want to know that?" she so innocently asks.

I smile at her and reply, "Because I want to do things that make you feel good and that you enjoy. For example, maybe you really enjoy having your neck kissed but don't like your ears licked. So I'll kiss your neck but not touch your ears. That's why I want to know what you like and don't like to have done to you. What turns you on when you think about it? How do you like your breasts touched? What are your fantasies? What is something you would like to try that you haven't? Things like that. If this is going to be based on being a sexual relationship, then we need to make sure its the best damn sex we can have so both of us get our needs met. I want to know what makes you feel good, and I will share with you what I like, okay?"

She sounds a little sad as she says, "I'm not sure what I like and don't like. I told you how sex was with my ex and other than some heavy petting and a few hand jobs with boys in school, I don't have any other experiences than him." She looks at me and almost pleading says, "So how can I tell you what I like if I don't know?"

I look up at the ceiling like I am thinking, and then, doing a very bad Sigmund Freud accent, I say, "Very interesting. It looks like we will need to do some more research." She laughs and using my regular voice, I say, "How about I take the lead today and see where it goes. You can tell me if you like something or not as we are doing it. Then, based on today, the next time you can tell me if you want to do something again or try something new. What you may want me to do more of or less of. Let's discover together what you like. And I do plan on making sure that you have an orgasm! I can tell it wasn't you that was the problem. You are moaning from just kissing me and if I had to bet, your pussy is already very wet."

She looks at me with big shocked eyes, "How did you know that ..... uh my pussy ... is wet. I feel like I am soaked down there. So I like the idea of you taking the lead to see where it goes. I have never had anyone ask me what I liked before."

"I'll say this once and never again. Your ex was a selfish little prick who doesn't know how to please a woman. All the things he said to you about sex were to cover up his own inadequacies. Done! So now, where were we? Oh yeah, we were kissing like this," and away we go again. It only takes a minute or two before she is moaning hard into my mouth and squirming on my lap. "Remember, you are going to tell me if you like something or not, right?" She nods an affirmative while barely breaking the kiss.

I slide my hands up the back of her shirt and to unsnap her bra. She giggles and says, "Uh uh, sports bra," and goes back to kissing me. I slide my hands around to the front to cup her breasts. I love her shape, her long, firm athletic frame, and that includes the small but firm breasts. Maybe no more than a B, but a delight to touch. I lift her bra up above her breasts and slide my hands back to cover them. I rub her breasts with my palms for a minute or two before I take my fingers and start playing with her nipples. They are small but firm and stick out to give me a lot to work with.

It only takes a couple of times circling her nipple with my finger to get another one of those wonderful little moans I so quickly learned to enjoy hearing. So next, I use just my right hand to lightly squeeze her nipple. Another moan. Then the left hand, same light-pressured pinch. Back to the right hand, I squeeze the nipple and then roll it around a bit with my fingers. "Oooh, that's nice,: she says, "I like that." I up the intensity with my left hand, a little harder pinch and and I squeeze her nipple a little harder as I roll it in my fingers. I am rewarded with a fuller, throatier moan and then, "Oh god. More."

I like hearing more. So she gets more, again the right hand starts rolling her nipple in my fingers, then I get her nipple between my thumb and finger, and as I squeeze it, I pull on it a little. I feel her shiver. Not releasing the right nipple, I do the same with the left. And as I squeeze it, I pull a little harder. As one of my favorite poets said, you never know what is enough until you know what is too much. I continue to squeeze both nipples harder than before as I pull a little further to see how far I can go before she says stop. I have her nipples out about an inch when she finally speaks. "God, I am enjoying this. I am so fucking turned on. Give me more." I am surprised to hear her say more. I was ready to hear that it was too much, but she wants more.

I wrap my arms around her and stand up. "Now, off to the bedroom, my lady." I carry her in and sit her down on the bed. I pull her shirt and bra off in one motion. She drops her arms across her chest and looks down, trying to cover up. I gently reach down and move her arms, pulling them away to expose her breasts and take a small step back. She looks up at me to see what I am doing. "Please, I want to look at you for a moment," I tell her. "I want to admire how beautiful you are." I can see her blush. After a moment of taking in her beauty, I step back up to her to grab her head with my hands, tilting her head up so I can kiss her. After a few moments of kissing, I drop to my knees.

I lean forward and use my tongue to give her right nipple a little lick. She shivers and moans. I lean over to the left nipple and do the same. Another moan. Back to the right and I suck her nipple into my mouth and use my tongue to swirl around it. She lets out a bigger moan. It seems she tries to both pull away and push her nipple deeper into my mouth. I move to the left and suck the nipple in, this time a little harder to see her reaction. More moaning, and then says, "I'm loving this." At some point, she has grabbed my head and is pulling me into her. I get her nipple good and wet and then I open my lips slightly to suck air into my mouth, like sucking on a straw, to pull cool air across her hot nipples. This draws a bigger moan and another "I like that too." I switch back and forth a few more times, increasing the pressure and intensity. The last couple, I am afraid, is too hard, but she just keeps moaning, and never stops me. I stand up and gently guide her to lie down on the bed, and then I join her. A couple of soft, quick kisses, "How are we doing?" I ask. Then teasingly say, "Ready to quit?"

"Fuck no" she says and wraps her arms tighter around me to pull me in closer. She grinds her crotch up against me and says, "I'm ready for whatever is next. What have you got for me, big boy?" I think, man, I like this girl. Hope I can keep up. I kiss her again, long and hard. As we are kissing, I start unfastening her pants. They are snug enough that I have to stop the kissing to be able to work her pants off. I make a point of taking off just the pants and leaving her panties on. To me, one of the sexiest looking things in the world is a woman in just her panties, and I am not disappointed. She has on a simple white thong.

Again, I take a moment to admire the view. "That, my dear, is one of the sexiest things I have ever seen. Do you know how beautiful you are?" She is lying there with one arm up on her forehead and the other just below those cut little tits. Her legs are crossed at the ankles. Someone should paint this and hang it in a museum, or in my bedroom. I reach down and grab a foot in each hand and slowly pull her legs apart. I lift one foot up and lick the inside of her arch. She shivers, so I lift the other and do the same. And I get the same response.

I lower her feet to the bed, making sure I have kept her legs spread far enough apart that I can crawl between them, because that's next on my plan. I lean down and run my tongue from her ankle to almost her knee. She moans and says, "I love how you are teasing me." I lean over to the other leg and start just below the knee and lick up the inside of her leg to mid-thigh. She looks at me, arm still on forehead but other hand has moved to her tit and she is squeezing her nipple, "You're evil" she laughs and then says, "You have me so turned on. Not sure what you have planned, but I am here for it."

I am now close enough to get a good look at the crotch of her panties and they are soaked. It looks like someone has poured water on them. I take it as a compliment. I move back to the other leg and starting mid-thigh, I run my tongue up and around the edge of her panties. She squirms, and I can see her rubbing her nipple a little faster. I move to the other side and start just a few inches from her panties and lick slowly up the edge of the leg hole, then move to the top of the panties to run my tongue across it. As I move my face down her panties, I drag my nose across her pussy. 'Oh god, stop teasing me," she moans.

She smells wonderful. There is nothing as great as the aroma of a turned-on woman, and this one is the best I have ever had. I gently lick across the front of those soaked panties. She pushes her pussy up at me but I am expecting it so I can move back and maintain that light teasing pressure. "Oh god, what are you doing to me?" I rub my nose a little harder against the panties up by her clit. Then I move down to run my tongue on either side of the panties on the inside of her thighs. She is wiggling and squirming, trying so hard for me to pay more attention to her pussy. "Please!" she moans, "please, I don't know how much more I can take."

I get my fingers under the waist band of her panties, then lift her ass enough that I can pull them down. She raises her feet in the air to help me get them off as easily as possible. She lowers her legs back down, spreads them, and says, "Please, I need you." She is ready for me to put my dick in her, but not yet. I lean forward and drag my tongue from the bottom of her pussy up to her belly button. I run my tongue around and then into her belly button, letting her know what could be next. I move my mouth back down and start gently licking her pussy. Running my tongue around the edges of her pussy lips, stopping for a moment to run my tongue at the top so see if I can find that little button of hers. One more trip around those tasty lips and back up to the top. The moaning is getting a little louder.

I push my tongue a little deeper this time and, bingo! I feel that little hard bump just inside. She jerks like I have touched her with ice or electricity or... well, something. I start paying extra attention to her clit. Running my tongue across it, first up and down, and then back and forth. Every so often I move my tongue lower and each time push my tongue a little deeper into her pussy, then I move back up. I start really working her clit over and start sucking at it. This causes her to start moaning almost non-stop. I slide my arm up underneath me so I can get my hand to her pussy. As I am licking her clit I slide a finger inside her. It is so wet, I pull back and add a second finger and it feels like her pussy is trying to suck my fingers inside her. I continue to suck and lick her clit. I look up, and she is pulling her nipples a lot harder and further than I did.

She keeps asking for more. So I slide my fingers almost out and decide to add a third as I push them back into her pussy. She continues to thrust against my hand as I use my tongue for all its worth. Suddenly she starts shaking, the moans turn to "Oh Fuck oh fuck on fuck what what what oh fuck. I'm coming." I suck as hard as I can and used my hand like a piston shoving those three fingers as deep and hard as I can. She reaches down and grabs the back of my head, trying to pull me deeper into her pussy. She is cumming so hard she is bucking off the bed. I think that she is going to break my nose or tear a finger off my hand. She cums for a long time and suddenly she squeezes her legs as tight as she can, trapping me between them and freezes, like a board. She shivers for a moment as the orgasms start to subside, then she starts to relax, releasing me. I slowly pull my fingers out of her pussy and my hand is completely soaked with her juices. I scoot up the bed and lie down beside her. She is still breathing pretty hard, and I give her a moment to catch her breath.

After a bit, she opens her eyes and looks at me, "What the fuck was that? No one has ever done that to me or made me cum that hard." I just smile at her, enjoying the moment. "No, seriously, I'm asking. What was that? How did you do that? It feels like I am still cumming."

I'm starting to catch on that she is serious. "You mean to tell me that no one has eaten your pussy before? Come on. Someone must have done that to you."

She shakes her head no, "Not like that! My ex, if he was a little drunk, might lick down there for moment but just to make sure it was wet enough, but no, NO ONE! has ever made me cum like that. That was amazing, earth-shattering. I would invite you over to do that every day, but I don't think I could take it every day."

I respond by looking directly into her eyes, "I am honored that I was the first to make you feel that way, but also disappointed that you haven't had that experience before. And as great as your pussy tastes I would be willing to do that every day." I bring my hand up to my lips to lick her pussy juice off my fingers while continuing to look her right in her eyes.

Shocking the shit out of me, she asks, "Can I taste that?" My eyes grow wide in disbelief at what she is asking. She continues, "I have tasted myself a few times when I have masturbated, but I wonder if this tastes different because of how hard I came. Is that weird?"

I quickly answer, "Nothing we do is weird if we both agree and like it." I slide my hand back down to her pussy to put two fingers back inside her pussy and move them around a bit.

She reaches down and grabs my hand, "Easy, cowboy, it's still a little sensitive down there." She grabs my hand to pull my fingers out and moves my fingers up to her mouth. She first licks one finger to get a taste then slides both fingers into her mouth and sucks her pussy juice off of them. She releases one of those great moans of hers. "Oh, I can see why you like it. It does taste different than when I am by myself. I want to taste a little more." And with that she leans over and starts kissing me, sucking my tongue and licking her juices off my face from around my mouth.

After a few minutes, we slow down and I say, "I think we need to hydrate, let's get something to drink, and we can come back.

She grabs my arm before I can move, looks me in the eyes, dead serious, and says, "Promise? Do you promise that we will come back? I'm not ready to be done." She looks down at her and then at me, "Besides, I am buck ass naked and you still have all your clothes on. Not fair."

I jump up off the bed and pull my shirt off and then take off my pants, leaving me in only my jockeys and my socks. "I Promise. See? Now I have to come back in here, if for no other reason than to get my clothes." She climbs out of bed, and we head off to get something to drink. I take notice that she has not put anything on and paddles off to the kitchen, beautifully naked.

As I watch that long, tall body, I mumble, "Thank you."